Methanol → (Z)-N-(1-(4-(4-Isopropylphenyl)phenyl)-1-(3-thienyl)prop-1-en-3-yl)sarcosine

HRID 433278Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13](/[C:16](/[C:29]3[CH:33]=[CH:32][S:31][CH:30]=3)=[CH:17]/[CH2:18][N:19]([CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[CH3:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].CO>C(O)=O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13](/[C:16](/[C:29]3[CH:33]=[CH:32][S:31][CH:30]=3)=[CH:17]/[CH2:18][N:19]([CH2:21][C:22]([OH:24])=[O:23])[CH3:20])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

(Z)-N-(1-(4-(4-Isopropylphenyl)phenyl)-1-(3-thienyl)prop-1-en-3-yl)sarcosine, t-butyl ester F(i) (18.62 g, 40.3 mmol) was dissolved in 96% formic acid (200 mL). The solution was warmed at 40° C. overnight, then concentrated. The residue was co-evaporated twice with CH2Cl2. Column chromatography (2-15% MeOH/CH2Cl2) provided a pale yellow solid. Trituration with methanol (MeOH) provided pure (Z)-N-(1-(4-(4-isopropylphenyl)phenyl)-1-(3-thienyl)prop-1-en-3-yl)sarcosine G(i) (11.38 g, 70%) as a white solid. 1H NMR (300 MHz, methanol-d4) 1.23 (d, 6H), 2.47 (s, 3H), 2.92 (hept, 1H), 3.26 (s, 2H), 3.50 (d, 2H), 6.22 (t, 1H), 6.94 (d, 1H), 7.32 (d, 4H), 7.46 (d, 1H), 7.57-7.65 (m, 5H).

Workup

concentrationconcentrated
customColumn chromatography (2-15% MeOH/CH2Cl2) provided a pale yellow solid

Sources & evidence

ORD record: ord-405d1822dd564941a99d6b5e78a59139
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06667336B2

Reaction notes

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